What To Look For In A Sailboat

Wow! Sounds like you had a good childhood. I definitely have the hull, engine and the rigging surveyed before making any purchase.

It was nice but as a kid I didn't know any different. I appreciate it more now. Found memories of my little brother and I playing with GI Joe dolls on the deck while we were underway, visiting different marinas up down the coast and meeting new girls in the marinas as we grew older.
Lots of Chuck Mangioni, Neil Diamond, and Lionel Richie. Good memories.

Good luck and hopefully you don't end up being one of those Woodsers who's always working on their boat every weekend instead of anchored out at the cape somewhere. Unless that's what you want to do of course.

I wish you the very best.